Polyvinyl alcohol, furfural, form-amide reaction product



Patented Mar. 15, 1849 UNITED STATES, PATENT OFFICE 7 2,404,717 POLYVINYL ALCOHOL, FURFUBAL, FORM- AMIDE REACTION PRODUCT Charles Arthur Porter, Believille, N. J., misnor to Resistoilex Corporation, Belleville, N. a corporation of New York No Drawing. Application December 28, 1945. l Serial No. 837,793

1 Claim. '(ci. zoo-1:)

This invention relates to polyvinyl alcohol compositions.

There'is a need in industry for materials having the great advantage which polyvinyl alcohol has of being inert toward hydrocarbon fuels and oils and organic solvents yet which has greater hardness, toughness, dimensional stability, tencut plasticizers in different amounts, with a view 'to-finding a product to meet the need above mentioned, I was surprised to discover what appears to be a reaction product possessing entirely new and advantageous characteristics but still possessing the peculiar advantages of polyvinyl alcohol. The exact nature of the resulting product is not known but it is thought probable that it is the result of a cross-linking of the polyvinyl alcohol molecules. 7

According to the invention, I have found'that sufliciently heating an admixture of completely saponified polyvinyl alcohol (known commercial- 131 as "Type B"), a small quantity of iormamide and a small quantity of furfural produces a prodnot unlike any heretofore known.

The copending application of Charles Dangelmaier, Ser. Ito/511,554, filed November 24, 1943,

now abandoned, discloses polyvinyl alcohol compositions containing formamide and paraform or other solid formaldehyde polymers, the latter being used in such amounts as to have a plasticizing effect on the composition, said application teaching the use of from 30 to 45 parts by weight of paraform to 100 parts of polyvinyl alcohol. In such compositions from 15 to 45 parts of formamide were found to improve the flowing properties of the compositions at elevated temperatures so as to make them readily moldable or extrudable. a

The present invention is to be distinguished from that of the above mentioned application in that the aldehyde, furfural, is here used in such small quantities as not to act as a plastieizer,

. the maximum amount being not over about 10%. basedon the polyvinyl alcohol. When so used.

in conjunction with a similarly small amount and the loss of thermoplastic properties.

2 of formamide, the composition, on being sulliciently heated. is converted into a product having entirely new properties. A temperature of at least 300 F. is used in molding to bring about the conversion and to produce a homogeneous product. Plasticizers commonly used in poll/- vinyl alcohol compositions, such as glycerol, glycerol'esters and water are used to give the product a desirable but limited degree of ilexibility and resiliency but they should not exceed in total amount, together with the aldehyde and iormamide, more than about 30% by weight of the total composition.

As a specific example of how the invention is to be practiced, a composition was prepared of the following ingredients, parts by weight:

Polyvinyl alcohol (completely saponified)- .Glycerol 20 Diacetin -i 3 Water it Formamide 5 Furfural 5 The glyceroL'diacetin and water are used as plasticizers to impart a limited degree of flexibility to the composition and the iormamid'e and iurfural are used as reactants with the polyvinyi alcohol.

The liquid components were admixed and then evenly distributed through the powdered polyvinyl alcohol by spraying on the powder while stirring. This moistened powder was formed into molded sheets in a heated platen press. To produce a homogeneous body by molding was found to require a temperature of at least 300 R When the mold was heated with steam under a gauge pressure of about lbs. per square inch, a sheet was produced which was black in color and which could not be remolded, showing that the composition was of a thermosetting nature. Reheating the sheet to the point where it charred produced no melting. Tests made on the composition, but omitting the iurfural, produced pre tically colorless sheets which would melt slightly on reheating. Omission of formamide alone from the composition also resulted in a colorless sheet which would melt slightly on reheating. It is therefore evident that when iurfural and formamide are both present, a reaction takes place as indicated by the change of color This change has never been observed in compositions containing plasticizing amounts of aldehydes or other plasticizers in the usual amounts, which are capable of being sintered or rendered homogeneous at much lower temperatures.

The resulting product has unusual toughness and while quite hard it has some flexibility. It

has very high tensile strength, high abrasive resistance, excellent fatigue characteristics, dimensional stability. good water resistance for a polyvinyl alcohol composition and no exudation whatever. At the same time the characteristic inertness oi polyvinyl alcohol toward hydrocarbon fuels and oils and organic solvents is retained unimpaired.

The composition has insufificient flowing prop erties, even when heated to maximum permissible temperature to permit of its being extruded and it must therefore be formed by molding. Mold- The foregoing detailed description is to be taken as illustrative oi the invention deflnedin the claims and not as a limitltion thereon.

What is claimed is:

The reaction product produced by. heating un-- .der pressure at a. temperature above 300' F.

completely saponified polyvinyl alcohol, iuriural. and iormamide, each in an amount oi from 2% to 10% of the Polyvinyl alcohol.

CHARLES ARTHUR PORTER.

narmmvcas CITED The following references are of record in the me of this patent:

-UNITED STATES PA'IENTS Number Name Date 2,037,049 $ager Apr. 14, 1936 2,083,628 Zelger June 15, 193'! 2,111,212 Paulson Mar. 15, 1938 -2,162,618 Izard June 13, 1939 2,340,866 Danzelmaler 1"eb.'8, 1944 2,399,401 Sonnichsen Apr. 30, 1946 2,399,450 Yates et al. Apr. 30, 1940 

